Project summary Organic molecules play an important role in a number of research areas relevant to human health, including biology, medicine, and drug development. One of the goals of synthetic organic chemistry is to facilitate discovery in these fields by providing access to organic molecules of increasing complexity and variety, and by expanding our ability to efficiently manipulate their structure and their properties. A critical part of the efforts toward this goal is the development of new organic transformations. The goal of the research described in this proposal is the development of two new classes of reactions: 1) anti-selective hydroalkylation of terminal alkynes. 2) Differential dihydrofunctionalization of alkynes. Once successfully developed, these transformations will greatly increase the complexity and versatility of products that can be obtained directly from alkynes. Considering the importance of alkynes as reactive intermediate in organic chemistry, this will have significant impact on the synthesis of biologically relevant compounds.